This uses just stock chipmunk and works without issue at a time step of 1/30 for 10 iterations. Momentum is MOSTLY conserved, but for my purposes this is ultimately going to lead to complex wall climbing behavior so I'm not too worried about it.

This uses a system of groove and pin joints, switching just at the right second to carry around corners. The only tricky part was maintaining connection information and determining when to constraint switch from joint A to joint B without stepping on the toes of the logic to switch the other way around.

This is old-ish, but an update to those who are interested. Thats just a poly shape pivot jointed to the staticBody, we drop a clingyBall on it and the rest is history. Much more to go from here, but I think this is a fairly original use for Chipmunk!